


Fitting

by Spn_kink_sock



Category: Supernatural
Genre: Alpha/Beta/Omega Dynamics, Consensual Underage Sex, Fondling, M/M, Nipple Play, Omega Dean, Parent/Child Incest, Plaid school girl skirts, Underage Sex, Vaginal Fingering, slutty dean
Language: English
Status: Completed
Published: 2018-08-26
Updated: 2018-08-26
Packaged: 2019-07-02 19:52:50
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,828
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15803451
Author URL: https://archiveofourown.org/users/Spn_kink_sock/pseuds/Spn_kink_sock
Summary: Another lj kink meme fill. The original prompt, edited for length.John takes Dean to be fitted for a bra and skirt and the salesperson takes the opportunity to check out the goods.John can watch or not be present at all. Sales clerk can be a man or a woman, original or known character.  Can be A/B/O if nonnie prefers.https://spnkink-meme.livejournal.com/109072.html?thread=40827664#t40827664Dean is underage, but not by much (nearly 18) and very enthusiastic about the whole situation.





	Fitting

"Dean, get out of the car! I don't have time for this."

His dad was about on his last nerve and Dean knew that, but he couldn't help himself. He had a damn good reason not to want to go to that particular store. The owner was a real creeper. She was this old Alpha lady named Gretchen and she claimed that she had to feel Dean up to get the right bra size for him. Never mind that he had just tiny little bitch tits and the it was always an A cup, just for nipple control. So Dean sulked in the back seat, refusing to get out, not caring that his father was on the verge of pulling him out of the back seat for an in the parking lot, over the knee bare assed spanking. 

"Dean, you need new bras for school and a new school uniform and I do not have time to deal with your bullshit. We have an hour to get it all done before we have to pick Sam up. You don't want him to try and walk home on his own again, do you?"

Sam had just popped his knot a few months ago at fourteen. Like all young Alphas, he thought he was indomitable. Thought he could stand up to everything, but there was a lot of sketchy territory between the Alpha high school and home. A lot of Alphas who thought they could build their status by taking down the weaker and the younger.

"Fine, but you're coming in the dressing room with me. Last time we were here, the owner got way too handsy.

Dean slid out of the backseat. Dad wouldn't really let Sam walk home alone if Dean didn't get this done. He didn't think. But Dad was also a stubborn bastard and he might just do it, just because he'd made the threat. Because an Alpha never went back on his word. Dean sighed and tugged his skirt down. School uniform for an Omega, was a short plaid skirt with a thin sweater top. If you didn't wear the bra, the slightest breeze would set off hardened nipples, which would just about pop right through the thin fabric. On weekends and afternoon, in the summers, Dean could wear his usual jeans and layers of thick shirts. Dad didn't care about that stuff. But for school, Dean was forced into Omega clothes. It was bullshit. He was almost eighteen and it was bullshit he was still forced to be in school at all.

He squared his shoulders and walked to the entrance of "Oh! Mega", the local Omega shop, the only place in town that sold the Omega school uniform.

"What do you mean, too handsy?" John asked.

"Like she said she had to measure my inseam and her tape measure got all up in my junk." Dean snapped, remembering how Gretchen had snickered as she'd slipped fingers into Dean's underwear, while keeping a light but steady finger on his submission gland, so he didn't have any choice but hold still. 

"Okay," Dad said. "I'll come in the fitting room with you."

The shop was different this time. It had been remodeled since the last time they'd been in. The prominent display by the entrance of sex toys, with the huge silicone knots in rainbow colors was gone. In it's place stood two smaller displays- one of nutritional supplements, the other of books about Omega health, Omega pregnancy and the like. The clothes right by the front had been the sleaziest, lacy-ist things you could imagine, all tawdry and synthetic. They'd looked sad and gross. They were gone, or banished to some back area of the store. Instead, the lead clothing displays were fresh, new looking. There were jeans even. Of course, they were paired with pink tops and more than a few had a built in Omega flap, but it was a vast improvement over the usual open cup bras and slit crotch panties that used to have top billing in the place. Dean glanced over at the counter where Gretchen usually kept watch, perched on a stool. No one was there at the moment, but a prominent sign at the counter announced that the place was under new management. 

After they'd been wandering around, looking for the school uniforms for less than a minute, a hulking Alpha male walked out from the back pushing a clothing rail filled with the school uniforms they'd been looking for. 

"Well, hello there, now. Welcome to Oh!Mega. What can I help you with today?" he asked, with a big smile. His eyes were a sparkling blue and his smile was kind and friendly. He didn't look like the sort of guy that would hold you down with your submission gland, but you never could tell. Damn, he was handsome though. Broad shoulders and a full beard. He looked like the kind of Alpha that never got a challenge because everyone knew they'd get a beat down. 

"What happened to Gretchen?" Dean asked, still suspicious of the man.

"Well, now, happens she's been wanting to retire for a while. She sold me this place and moved to Florida. I'm Benny."

"We need three school uniform skirts and a handful of bras for the boy," John said. "We don't have a lot of time to waste. He's grown a lot in the last year, so I don't know what size he needs. Especially in the."

John didn't finish his sentence, but instead swooped his hands over his chest, the universal gesture for tits apparently. Dean flushed with embarrassment. He hadn't grown that much. They were definitely still what he would call little. In fact, he'd been fingering some knit fabric bralets hung on a display nearby. They were a plaid print and sports bra style. 

"Ah, no, Chief," the new owner said. "You've outgrown those, I'm afraid. Definitely time for a full support system for you. You are well on your way to becoming the curvy Omega of some lucky Alpha's dream. Here. I'll grab a few things that might work and I'll meet you in the dressing room over there."

"You some kind of faggot?" Dad suddenly demanded of the new owner. He was probably the only Alpha Dean knew that wouldn't think twice about challenging an Alpha of Benny's obvious size and prowess.

"Oh, you mean because I bought a clothing store?" Benny asked, with a smile. "Just gonna ask you, Chief, can you think of another business where an Alpha is going to meet as many young and lovely Omegas as this one?"

A few minutes later, all three of them were in the biggest dressing room in the place. It had been freshly painted in pink with new white carpeting. There was a big leather chair to one side that had an "Alpha Parking" sign on the wall above it. There was a clothing rail loaded with Benny's selections. There was a white chaise lounge nearby the three way mirror. The place was well lit, not with the overhead florescent bar lights it had before, but with crystal loaded wall sconces and a little crystal chandelier above. Dad looked around and snorted, but took his place on the big leather chair. 

In the close quarters, Benny's Alpha scent, previously just kind of in the back ground, intensified. It was like the sea and sand. It was salt water and freshness itself. It was sunny and warm too. It smelled good. Enticing. If Dad wasn't just right there, a baleful presence in the corner, Dean might have flirted a little. Okay. A lot. Cause the dude was hot. Just the kind of Alpha Dean wanted some day. 

"Why don't you try on one of those skirts first and then we'll see where we're at, if we need to getcha in something longer."

Dean pulled one of the plaid skirts over his head then tugged it down into place. He undid his current uniform skirt and let it drop to the floor. The new skirt came down to well below his knees. 

"Well, part of the problems is that skirt ain't supposed to sit at your lower hips," Benny said. "I think it's just far too big on you, waist size and everything."

He stepped up behind Dean and laid his hands of Dean's hips. His hands were huge and spanned most of Dean's backside, so the big Alpha's thumbs rested at the top of Dean's ass crack. After a moment, he lifted and tugged at the skirt, pulling it up and back. The excess fabric was gathered and pulled out of the way. The skirt's waistline settled at Dean's natural waist. The skirt hem rose to above Dean's knees and it looked exactly how it was supposed to. 

"You're such a slender little thing. Gonna need a much smaller size," Benny said.

"Let's try this one," he said. He pulled a skirt that looked no bigger than a doll's skirt from the rack. "Nah, that's too short. We want you to look pretty, not trashy. Here we go."

He motioned Dean to step into the skirt and slid it up Dean's body, his hands traveling smoothly over Dean's thighs. They were strong, steady and sure. If Dean's dad weren't sitting right across the room, looking bored as hell, Dean might have melted into that touch because this shop owner could touch Dean any time he wanted. Benny's hands undid the fastener to the too big shirt and let it slip to the floor where it puddled around Dean's ankles.

He stood right behind Dean, hands on Dean's hips and pulled Dean back, just a little. The shop owner was more than a little interested in Dean too. That or he had an enormous flashlight in his front pocket. 

"Now, I bet you like the size of that, don't you, Cherie?" he asked. "Fit you like a glove."

If only Dad weren't sitting on the other side of the room. He wasn't watching. In fact, he'd pulled out an old and crumbly history book from his bag. He might have been a mechanic and owned a garage but John Winchester had a strange liking for mythology and lore of all cultures. 

"Yeah, I like it a lot," Dean said. Actually, the fit of the skirt was perfect and came just an inch over his knees, so it wasn't trashy, but it wasn't like he was some forty-five year old Omega matron either. "You got anything else I could try on?"

"Your Daddy said you needed some bras, didn't he?" Benny said, moving his hands up from Dean's waist to the inside of Dean's sweater. "That little thing you're wearing now don't do justice to what you've got. They're not big, mind, but they've got a certain fullness to them. Have to learn to keep them under control."

Benny's fingers found Dean's nipples and he pinched them lightly. Dean had to bite his lip from gasping in pleasure. Benny's hands held Dean's little breasts gently, as if they were peaches or some other fruit that could be easily bruised. He massaged them, teasing and arousing Dean. 

Dad still had his nose buried in the book, no clue what was happening as Benny played Dean's body masterfully. He didn't have to tell Dean to keep quiet. Dean shoved a fist into his own mouth to stop himself from crying out. Then slowly, John Winchester's normal tiredness caught up with him. As Benny fondled Dean's tits, John's eyes slowly shut and his chin dropped to his chest. He was a single father to two boys and ran his own business. He deserved a nap, didn't he? And it was convenient for Dean.

As soon as it became clear that John was out, Benny moved one of his hands south. It dipped between Dean's legs, rubbing and seeking.

"Can't risk knotting you with your old man there, having a snooze," Benny whispered. "You want me to make you come though?"

Dean nodded. Benny's answer was a finger deeper into Dean's cunt. It dipped inside of Dean, pumping in and out, finding Dean's o-spot immediately. There were bright sparks of pleasure now adding to the burn as Benny's finger brushed against it again and again. 

"You want me to hit your o-gland?" he asked, still in a whisper. "Some boys like that, some don't."

Dean hated it. It reminded him of the Gretchen's of the world, who didn't ask first. "Don't touch it, please."

"You got it, cher."

"No. Oh. Yes, so good," Dean murmurred as Benny had started a faster rhythm, now tugging harder and faster on the nipple still in his one hand. "Just keep that up. Oh. Yes."

Dean had to brace himself on the edge of the chaise as Benny moved faster and faster, crooking his finger inside of Dean, then adding another, which was all that Dean needed. Everything went white and staticky in his head and his whole body clamped down and it was wonderful. 

And John Winchester was still asleep in the fitting room chair, lightly snoring. How could he not notice that Dean had just come. Even Dean could smell his own Omega slick, cloying and thick. He hadn't just come. He'd squirted a little. There was a small puddle of it on the floor. Benny's hand was damp and he was licking the slick off his fingers, savoring it. He looked satisfied, even though his pants were still tented out with his knot.

Dean turned around and reached for Benny's waistband, but the man stopped him. 

"We mostly likely don't have time for anything else before your old man wakes up. I'm satisfied to have provided a service you needed."

"Now, about those bras you need," Benny said. "How about this one."

He held up a small confection of beige colored lace. There were curved underwires covered with cloth, but the rest was mesh and floral, with just enough fabric to cover Dean's nipples. There were two thin ribbons that connected the underwires and lace part to the straps. 

"It's called a cage bra. It's the latest thing and just enough support without being too much," Benny said. A moment later, they had Dean's sweater off and Benny was fastening him into the contraption. There were hooks that did up and straps that were placed here and there. Then Benny had Dean lean over and he reached right into Dean's bra cups and pulled Dean's tits into place, settling them just so. 

"Like I thought. A perfect fit."

The history book finally dropped off Dad's lap and he startled awake. John Winchester's sleepy disorientation only lasted a few seconds though. A moment later, he stood up and walked across the room to Dean. He laid his hands on Dean's breasts and hefted them a little, rubbing Dean's breasts through the fabric.

"Very nice," he said. "Very pretty. I like this one. Get him about four more just like this one. He'll wear this one out today."

"I'll have to order them," Benny said. "I've only got this one in this size. Can get them by next week if that's good with you."

"I'll send Dean by himself to pick them up," Dad said. He tweaked Dean's nipple, just a little too hard. "I think he'd like that."

"I will say it's a pleasure doing business with you both."

Later that night when Dean was speared on his Daddy's knot, wearing nothing but the lace cage bra, John said, "Did you just let him touch your pussy or did you let him slip you his cock, Baby?"

They were on the sofa in the living room, John sitting up on the sofa, Dean thighs spread over his lap. John's big hands spanned Dean's waist and even though they were tied together John bounced Dean lightly up and down on his knot, not enough to tug at the rim, but enough to grind his knot deep again't Dean's o-spot. 

"He just fingered me, Daddy," Dean confessed. "It felt so good."

"Little slut," John said, but it was fondly. Still, he slapped Dean hard on the ass, enough to sting. "You going to let him put that knot of his up in your slutty pussy when you pick up the rest of your things next week.

"Yeah," Dean said. "If he wants to give it to me."

"I thought you didn't like getting felt up by fitting room clerks."

"I don't like getting felt up by jerks who don't ask first," Dean said, as his Daddy slapped his ass again. 

"Mmmm, such a slutty boy for me," John said. "Did you keep your old skirt, the one you're growing out of?"

"Yeah, but I can't wear it to school anymore," Dean said. "They sent me home for that, remember?"

"I was thinking for wearing around the house," John said, nuzzling his face into Dean's breasts.


End file.
